Ammonia → 2'-Deoxy-2'-fluoro-2'-methyluridine

HRID 1526103Notes

Reaction equation

HRID 1526103 reaction equation
C([C@@:9]1([OH:34])[C@@H:13]([CH:14](C(=O)C2C=CC=CC=2)[OH:15])[O:12][C@@H:11]([N:24]2[CH:31]=[CH:30][C:28](=[O:29])[NH:27][C:25]2=[O:26])[C@@:10]1([F:33])[CH3:32])(=O)C1C=CC=CC=1.N>CO>[F:33][C@:10]1([CH3:32])[C@H:9]([OH:34])[C@@H:13]([CH2:14][OH:15])[O:12][C@H:11]1[N:24]1[CH:31]=[CH:30][C:28](=[O:29])[NH:27][C:25]1=[O:26]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86638038HCID 86638038, compound

Product 1

HCID 113115032'-Deoxy-2'-fluoro-2'-methyluridineYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3′,5′-dibenzoyl-2′-Deoxy-2′-fluoro-2′-C-methyluridine (1.5 g, 1 eq) in MeOH (10 mL) was added a solution of saturated ammonia in MeOH (20 mL). The reaction mixture was stirred at 0° C. for 30 min, and then warmed to room temperature slowly. After the reaction mixture was stirred for another 18 hours, the reaction mixture was evaporated under reduced pressure to give the residue, which was purified by column chromatography to afford pure compound 2′-deoxy-2′-fluoro-2′-C-methyluridine (500 mg, Yield: 60%).

Workup

  1. temperaturewarmed to room temperature slowly
  2. stirringAfter the reaction mixture was stirred for another 18 hours
  3. customthe reaction mixture was evaporated under reduced pressure
  4. customto give the residue, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a05109dc2e15481fb681eb2eedb1adaf
Source dataset
uspto-grants-2015_07
Patent number
US09085573B2

Reaction notes

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